People in their 60s don’t talk about it much, but plenty of them are slipping their otherwise able adult children money on the side. Sometimes, lots of money, very often. So Cheryl R. Holland, a financial planner in Columbia, S.C., tries to approach the topic delicately but deliberately: May we discuss how you might transition them to financial independence?

She uses the “may” because sometimes one spouse is an enabler, and the other has asked her to intervene. At other times, she’s not sure whether a client is truly ready to confront the fact that they’ve raised a 37-year-old who is consistently unable to earn a living.

Then there’s the “might” element. “What parents want is financially independent children, but if they’re not willing to let them fail, sometimes pretty wildly, by the time they’re in their 30s, then you’re going to be 70 and giving them money,” she said. “And that can impinge on your own ability to retire.”

Ms. Holland’s use of the conditional also allows for the fact that some retirees get more joy from paying for their grandchildren’s tuition than they will from anything else.

“I have one family that looks at me cheerfully and says that they’re not going to stop,” she said. “I ask if I can keep asking them each year, and they say yes, but the answer is not going to change.”